How to Talk To Your Team About Failure

A story about being very very direct.

William Anderson
Oct 9, 2019 · 4 min read
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As soon as I saw the feature in production I knew we had failed. I knew deep down from the surface to the darkest depths. The feature didn’t work as expected. The team knew it was broken before it’s release. I didn’t catch it. They didn’t stop it. The fix for it was relatively small but would take a couple of days before we would be able to roll it out. I knew that that wouldn’t matter to users.

When you are using a website and something is broken, you don’t think:

“Well, I’m sure they will fix this broken feature in a day or so and it's okay, because I assume its just an easy fix anyway.”

When you are using a website and something is broken, you think:

“Wow, this is trash, how could they not have seen this?” and then you close the tab.

My first instinct was to focus on the positive. We shipped it. We hit the deadline. We didn’t drown ourselves in overtime doing it. This was all true. It was also the wrong message.

A bit late I gave a pretty good speech to the team where I espoused the values of caring for the user, and how we needed to embrace this as a failure so that we could come together, fix what was wrong and move towards successes we could celebrate.

I default to positive and find ways to celebrate success even in failure. My struggle is that while celebrating accomplishments is key to helping a team gel and build morale, facing mistakes honestly and candidly is even more crucial.

When a feature or product fails, coming together to make each other feel better just soothes egos. Coming together and talking about how you failed solves problems.

Ownership, not just by individuals but by teams is critical towards delivering software of value. In this case, we all needed to feel the impact of failure, and each team member needed to find a way they could feel empowered to prevent a similar failure in the future.

Every team can benefit from looking at their sugar-free reality. The key is looking to reality in a way that is both blameless as well as corrective. Here is how you can ensure you do the same with your teams.

1. Make it clear that you don’t see success.

This is the most emotionally draining.

All the hard work has been done, late nights had and the work released. Maybe it was rolled back right away, maybe it was delivered 6 months late, maybe you don’t have enough functionality to even attempt to secure funding, but regardless you know it wasn’t a success. Pull your team together and tell them.

This isn’t an easy task neither is it a conversation. Don’t yell at your team, don’t be angry, you are one of them too and your tone should convey that. Let them know you don’t see the project as a success and let them know why. Let them know what you wish you had, or what you wish hadn’t happened. Let them know just as well how you feel you yourself could have done better. Finally, let them know that there will be a post-mortem to talk about it later.

After sharing, go around for updates on what each person is doing now to move you all towards success. Either fixing existing problems or getting work done. If you consider the work a failure, it means it's not good enough, you can’t stop if you still plan on delivering.

2. Let the team digest.

Give the team time to digest your message and even approach you one-on-one. Be available and be honest with them. In many conversations I’ve had in this type of situation, I’ve even been as explicit to say “I’m not angry or upset, but I felt it was important that as a team we felt how we failed, which is why I expressed that the way I did. I want to see the success in what we did, but I know its more important for us to acknowledge the failure.”

If someone wants to know how their particular role didn’t measure up, likewise be constructive and let them know the difference between reality and expectations.

3. Hear out the teams reflections.

Hold a retrospective on the work and what happened. Ideally, have a neutral party run it, but be present. Your team may hold back while you are there, but hopefully, they trust you enough to open up. Here it's fine for there to be explanations, reflections, maybe even excuses, but never blame.

4. Make success.

Overcome your failure, and fix it. Or drop it and pivot, but move forward and make success. Once you find it, celebrate! The story of how you failed and then came together will help you all grow.

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